ES2206840T3 - Derivados del antibiotico a82846b (cloroorienticina a). - Google Patents

Derivados del antibiotico a82846b (cloroorienticina a).

Info

Publication number: ES2206840T3
Authority: ES; Spain
Prior art keywords: compound; alkyl; formula; phenyl; present
Prior art date: 1997-05-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES98303495T

Other languages

English (en)

Spanish (es)

Inventor

Richard Craig Thompson

Stephen Charles Wilkie

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eli Lilly and Co

Original Assignee

Eli Lilly and Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-05-20

Filing date

1998-05-05

Publication date

2004-05-16

1998-05-05 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

2004-05-16 Application granted granted Critical

2004-05-16 Publication of ES2206840T3 publication Critical patent/ES2206840T3/es

2018-05-05 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 claims abstract description 30
-1 p- (p-chlorophenyl) benzyl Chemical group 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
238000000034 method Methods 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
208000035143 Bacterial infection Diseases 0.000 claims description 6
208000022362 bacterial infectious disease Diseases 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 5
125000001475 halogen functional group Chemical group 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 2
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
229940079593 drug Drugs 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
239000012454 non-polar solvent Substances 0.000 claims description 2
150000007524 organic acids Chemical class 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
241000194033 Enterococcus Species 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
MYPYJXKWCTUITO-KIIOPKALSA-N chembl3301825 Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)C(O)[C@H](C)O1 MYPYJXKWCTUITO-KIIOPKALSA-N 0.000 claims 1
239000003085 diluting agent Substances 0.000 claims 1
239000000825 pharmaceutical preparation Substances 0.000 claims 1
229940127557 pharmaceutical product Drugs 0.000 claims 1
230000000844 anti-bacterial effect Effects 0.000 abstract description 9
108010015899 Glycopeptides Proteins 0.000 abstract description 6
102000002068 Glycopeptides Human genes 0.000 abstract description 6
DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical compound NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 abstract description 4
239000007858 starting material Substances 0.000 abstract description 4
229940088710 antibiotic agent Drugs 0.000 abstract description 3
125000001909 leucine group Chemical group [H]N(*)C(C(*)=O)C([H])([H])C(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
230000015556 catabolic process Effects 0.000 description 4
238000006731 degradation reaction Methods 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
208000015181 infectious disease Diseases 0.000 description 4
239000000203 mixture Substances 0.000 description 4
QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 4
238000002953 preparative HPLC Methods 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
239000003643 water by type Substances 0.000 description 4
241000894006 Bacteria Species 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
239000012043 crude product Substances 0.000 description 3
239000002243 precursor Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
239000002904 solvent Substances 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
238000010828 elution Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
150000002540 isothiocyanates Chemical class 0.000 description 2
229940117953 phenylisothiocyanate Drugs 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000002560 therapeutic procedure Methods 0.000 description 2
238000000825 ultraviolet detection Methods 0.000 description 2
241000192125 Firmicutes Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 1
125000000729 N-terminal amino-acid group Chemical group 0.000 description 1
108010053950 Teicoplanin Proteins 0.000 description 1
108010059993 Vancomycin Proteins 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
238000002815 broth microdilution Methods 0.000 description 1
DDTDNCYHLGRFBM-YZEKDTGTSA-N chembl2367892 Chemical compound CC(=O)N[C@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1O[C@@H]([C@H]1C(N[C@@H](C2=CC(O)=CC(O[C@@H]3[C@H]([C@H](O)[C@H](O)[C@@H](CO)O3)O)=C2C=2C(O)=CC=C(C=2)[C@@H](NC(=O)[C@@H]2NC(=O)[C@@H]3C=4C=C(O)C=C(C=4)OC=4C(O)=CC=C(C=4)[C@@H](N)C(=O)N[C@H](CC=4C=C(Cl)C(O5)=CC=4)C(=O)N3)C(=O)N1)C(O)=O)=O)C(C=C1Cl)=CC=C1OC1=C(O[C@H]3[C@H]([C@@H](O)[C@H](O)[C@H](CO)O3)NC(C)=O)C5=CC2=C1 DDTDNCYHLGRFBM-YZEKDTGTSA-N 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
XJHXLMVKYIVZTE-LOALFDMRSA-N chloroeremomycin Chemical compound O([C@@H]1C2=CC=C(C(=C2)Cl)OC=2C=C3C=C(C=2O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O[C@@H]2O[C@@H](C)[C@H](O)[C@@](C)(N)C2)OC2=CC=C(C=C2Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]2C(=O)N[C@@H]1C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@@H](O)[C@H](C)O1 XJHXLMVKYIVZTE-LOALFDMRSA-N 0.000 description 1
108700026803 chloroorienticin A Proteins 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
150000002016 disaccharides Chemical class 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
229960003085 meticillin Drugs 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
239000007787 solid Substances 0.000 description 1
241000894007 species Species 0.000 description 1
229960001608 teicoplanin Drugs 0.000 description 1
150000003585 thioureas Chemical class 0.000 description 1
229960003165 vancomycin Drugs 0.000 description 1
MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
MYPYJXKWCTUITO-LYRMYLQWSA-O vancomycin(1+) Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C([O-])=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)[NH2+]C)[C@H]1C[C@](C)([NH3+])[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-O 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/006—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure
- C07K9/008—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence being part of a ring structure directly attached to a hetero atom of the saccharide radical, e.g. actaplanin, avoparcin, ristomycin, vancomycin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biophysics (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
General Chemical & Material Sciences (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

ES98303495T 1997-05-20 1998-05-05 Derivados del antibiotico a82846b (cloroorienticina a). Expired - Lifetime ES2206840T3 (es)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US4716597P	1997-05-20	1997-05-20
US47165P		1997-05-20

Publications (1)

Publication Number	Publication Date
ES2206840T3 true ES2206840T3 (es)	2004-05-16

Family

ID=21947405

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES98303495T Expired - Lifetime ES2206840T3 (es)	1997-05-20	1998-05-05	Derivados del antibiotico a82846b (cloroorienticina a).

Country Status (11)

Country	Link
US (1)	US5952310A (de)
EP (1)	EP0879825B1 (de)
JP (1)	JP4150430B2 (de)
AT (1)	ATE250082T1 (de)
AU (1)	AU7284798A (de)
CA (1)	CA2290724C (de)
DE (1)	DE69818144T2 (de)
DK (1)	DK0879825T3 (de)
ES (1)	ES2206840T3 (de)
PT (1)	PT879825E (de)
WO (1)	WO1998052596A1 (de)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ATE361931T1 (de) *	1998-05-01	2007-06-15	Lilly Co Eli	N1 modifizierte glycopeptide
ATE242783T1 (de)	1998-12-23	2003-06-15	Theravance Inc	Glycopeptid-derivate und pharmazeutische zusammensetzungen, die sie enthalten
JP5178520B2 (ja)	2005-09-22	2013-04-10	メディバスエルエルシー	固体ポリマー送達組成物およびその使用法
EP1926780B1 (de)	2005-09-22	2013-08-14	Medivas, LLC	Bis-( -amino)-diol-diester-haltige poly(esteramid) und poly(esterurethan)-zusammensetzungen und verwendungsverfahren
US8841440B2 (en)	2008-04-01	2014-09-23	Cornell University	Organo-soluble chitosan salts and chitosan-derived biomaterials prepared thereof
CN102250221A (zh) *	2010-05-19	2011-11-23	复旦大学	万古霉素类衍生物及其制备方法和用途

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4698327A (en) *	1985-04-25	1987-10-06	Eli Lilly And Company	Novel glycopeptide derivatives
US4643987A (en) *	1985-08-14	1987-02-17	Eli Lilly And Company	Modified glycopeptides
EG18377A (en) *	1986-09-19	1993-04-30	Lilly Co Eli	Process for preparing glycopeptide antibiotics
US5534420A (en) *	1988-07-28	1996-07-09	Eli Lilly And Company	Biotransformation of glycopeptide antibiotics
ATE160360T1 (de) *	1989-07-18	1997-12-15	Biosearch Italia Spa	Aus dalbaheptide hergestellte pentapeptid- antibiotika
CA2031803C (en) *	1989-12-13	2001-05-29	Ramakrishnan Nagarajan	Improvements in or relating to glycopeptide deriveratives
TW213468B (de) *	1991-06-29	1993-09-21	Hoechst Ag
AU703106B2 (en) *	1994-01-28	1999-03-18	Eli Lilly And Company	Glycopeptide antibiotic derivatives
US5919756A (en) *	1996-06-28	1999-07-06	Eli Lilly And Company	Amides

1998
- 1998-04-30 US US09/070,072 patent/US5952310A/en not_active Expired - Fee Related
- 1998-05-05 WO PCT/US1998/009115 patent/WO1998052596A1/en not_active Ceased
- 1998-05-05 ES ES98303495T patent/ES2206840T3/es not_active Expired - Lifetime
- 1998-05-05 DE DE69818144T patent/DE69818144T2/de not_active Expired - Fee Related
- 1998-05-05 CA CA2290724A patent/CA2290724C/en not_active Expired - Fee Related
- 1998-05-05 DK DK98303495T patent/DK0879825T3/da active
- 1998-05-05 AU AU72847/98A patent/AU7284798A/en not_active Abandoned
- 1998-05-05 JP JP55040298A patent/JP4150430B2/ja not_active Expired - Fee Related
- 1998-05-05 PT PT98303495T patent/PT879825E/pt unknown
- 1998-05-05 EP EP98303495A patent/EP0879825B1/de not_active Expired - Lifetime
- 1998-05-05 AT AT98303495T patent/ATE250082T1/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
EP0879825A3 (de)	1999-11-24
ATE250082T1 (de)	2003-10-15
US5952310A (en)	1999-09-14
DE69818144D1 (de)	2003-10-23
JP2001526681A (ja)	2001-12-18
AU7284798A (en)	1998-12-11
WO1998052596A1 (en)	1998-11-26
CA2290724A1 (en)	1998-11-26
CA2290724C (en)	2010-03-23
DE69818144T2 (de)	2004-07-15
PT879825E (pt)	2004-02-27
JP4150430B2 (ja)	2008-09-17
EP0879825B1 (de)	2003-09-17
EP0879825A2 (de)	1998-11-25
DK0879825T3 (da)	2004-02-02

Publication	Publication Date	Title
ES2202746T3 (es)	2004-04-01	Hexapeptidos alquilados como antibioticos.
US5912226A (en)	1999-06-15	Anhydro- and isomer-A-21978C cyclic peptides
EP0816378A1 (de)	1998-01-07	Derivate von Amiden glycopeptidischer Antibiotica
JP3418762B2 (ja)	2003-06-23	抗生物質ａ４０９２６のアミド誘導体類
US7632918B2 (en)	2009-12-15	Semi-synthetic glycopeptides with antibiotic activity
ES2206840T3 (es)	2004-05-16	Derivados del antibiotico a82846b (cloroorienticina a).
ES2283107T3 (es)	2007-10-16	Glicopeptidos modificados en n1.
EP0801075A1 (de)	1997-10-15	Kovalentgebundene Dimere von Glykopeptid-Antibiotika
ES2206839T3 (es)	2004-05-16	Derivados de urea de tiourea de glicopeptidos antibioticos.
KR20110099028A (ko)	2011-09-05	항세균제로서의 신규 반-합성 글리코펩티드
US4335111A (en)	1982-06-15	Compounds associating peptidyl of aminoacyl residues to lipophilic groups and pharmaceutical compositions containing said new compounds
Preobrazhenskaya et al.	2004	Patents on glycopeptides of the vancomycin family and their derivatives as antimicrobials: January 1999–June 2003
US9481712B2 (en)	2016-11-01	Peptidomimetics possessing photo-controlled biological activity
KR100298136B1 (ko)	2001-10-24	합성아글루코달바헵티드항생제
JP3126981B2 (ja)	2001-01-22	アグルコテイコプラニンから誘導されるヘキサペプチド及びその製造法
US20170051017A1 (en)	2017-02-23	Peptidomimetics possessing photo-controlled biological activity